Something old is now something new in a lollipop pumpkin pie

By Jim Bailey

As a child I ate pumpkin pie, but begrudgingly. It wasn’t because I didn’t enjoy the taste, it was just a little bland for my sweet tooth. But “in the day,” when food was put in front of you, you ate it. Having aged slightly, I enjoy the aroma of clove-scented baked pumpkin pie wafting through the entire house, mingling with the savory smell of yeast-risen bread (yes, we still make our own bread for the holidays), the salty tinge hanging in the air from the glazed ham roasting and the always present, pleasant bouquet of cranberry potpourri sneaking around each room.
The only thing that’s missing is the dry, hardwood crackling from the living room and kitchen as it toils to heat everyone and cook everything in both the fireplace and wood cookstove. In the meantime, if I don’t give you this recipe, I am going to keep on reminiscing and won’t get a thing done.

Pumpkin Pie Lollipops

These little mini pies are truly a treat for the kids after school or make a pile of them for your holiday gathering. If you prefer, you can make mini apple pies. Simply put 2 c. diced apples, 1 c. apple juice or cider, 1/4 t. cinnamon, a pinch each of nutmeg, ginger and allspice in a saucepan over medium-high heat and cook until apples are almost soft, 4 to 6 minutes. Remove to bowl to cool to tepid and fill each lollipop according to instructions. Want a dip for the mini apple pies? Mix 1 c. pureed pumpkin with 1/2 c. creme fraiche or plain yogurt and 1/4 c. caramel topping. Mix well and there you have it.
You can substitute 2 t. pumpkin pie spice instead of the cinnamon, ginger and cloves if desired.

1 recipe (for 2 crust pie shell) pie pastry
1(15 oz. can) pure pumpkin
3/4 c. sugar
1 t. cinnamon
1/2 t. salt
1/2 t. ground ginger
1/4 t. ground cloves
Coarse sugar
Apple cider glaze, recipe below
Flat popsicle (craft) sticks

In a bowl, combine pumpkin, sugar, cinnamon, salt, ginger and cloves. Stir until well blended; set aside. Preheat oven to 375-degrees F. Roll out the pie dough a little thinner than you ordinarily would for pies. With any round shaped cutter, cut out two circles for each lollipop you are making. Line a baking sheet with parchment paper or use a nonstick baking sheet. Place one round of dough on the pan for each lollipop. Place a popsicle stick onto circle of dough, with about half an inch laying on the dough. Dollop 1 T. pumpkin filling into the center of each round and cover with second circle of dough. Flatten with the tines of a fork to seal, brush with milk and sprinkle liberally with coarse sugar. Bake for 15 to 18 minutes, or until slightly browned. Remove from oven and cool 10 minutes before removing to a rack or platter. Serve with apple cider glaze.

Apple Cider Glaze
2 c. apple cider
Pinch ground cloves

Bring to a boil over high heat, stirring occasionally, and continue boiling 8 to 12 minutes or until reduced by half and syrupy. Let cool slightly before dipping your Lollipop Pie into it.

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Filed Under: Community and Arts LifeThe Yankee Chef

About the Author: Jim Bailey is a third generation Yankee Chef, New England food historian and newspaper columnist. His first cookbook, simply titled The Yankee Chef, has been published. He welcomes all feedback, questions or comments at

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